The present invention relates to a fragrance having a 2-cyclohexyl-1,1-dimethyl ethanol derivative represented by formula (1) 
wherein R represents a hydrogen or an acetyl group, Me represents a methyl group, and n represents an integer from 0 to 3.
In addition, the present invention relates to a fragrance composition containing as an active component a fragrance comprising one or two or more types of 2-cyclohexyl-1,1-dimethyl ethanol derivative represented by the above formula (1). The present invention also relates to an aromatic bleaching composition containing this fragrance composition.
In recent years, with the increasing variety in various perfume products and sanitation products, there are a variety of expectations for fragrances useful for adding scents to these products. Fragrances that provide a pleasant scent, or fragrances that have a very distinctive and agreeable scent, have been sought. Furthermore, there has been increasing demand for fragrances that match the characteristics of individual products. At the same time, in terms of the properties of the fragrance itself, there is a need for fragrances that are chemically stable, while mixing well with other fragrances.
To satisfy these demands, it has always been very important for the fragrance industry to develop and provide fragrance materials that have both individual distinctive characteristics as well as an agreeably pleasing scent.
U.S. Pat. No. 4,006,218 discloses a 2-cyclohexyl-1,1-dimethyl ethanol compound. This compound is used together with an anti-microbial agent, such as cetyl pyridinium chloride, which is commonly used in anti-microbial compositions to increase the anti-microbial action. In addition, Japanese Laid-Open Patent Publication Number 2-31683 discloses 2-cyclohexyl-1,1-dimethyl ethanol as an active component of a pest repellent.
As disclosed in Japanese Examined Patent Publication Number 7-65067, the scent characteristic of 4-cyclohexyl-2-methyl-2-butanol is effective in developing a floral fragrance that is reminiscent of lily of the valley. Methods are disclosed for providing, improving, or modifying the floral fragrance by mixing the compound with other fragrances. Furthermore, Japanese Laid-Open Patent Publication Number 7-238297 discloses 2-cyclohexyl-2-propylesters as fragrance compounds.
However, there are no descriptions of the scent characteristics of 2-cyclohexyl-1,1-dimethylethanol compounds and their acetates and the like. In addition, there are no descriptions of methods for using these compounds as fragrance materials used in adding scent to various perfume products and sanitation materials.
It is an object of the present invention to provide a fragrance material that overcomes the foregoing problems.
It is a further object of the present invention to provide a fragrance material that is very pleasing and satisfies the requirements corresponding to the product characteristics, that has excellent stability in the product, and that can be mixed well with other fragrances.
It is still a further object of the present invention to provide a fragrance composition comprising this fragrance material as an active component.
It is another object of the present invention to provide a method for using this fragrance composition.
As a result of intensive research to attain the above objectives, the present inventors have discovered that 2-cyclohexyl-1,1-dimethyl ethanol derivatives have a pleasing and highly unique scent, are chemically stable, and have excellent harmony with other fragrances. The present invention includes each of the following embodiments:
(1) A fragrance comprising a 2-cyclohexyl-1,1-dimethyl ethanol derivative represented by formula (1) 
wherein R represents a hydrogen atom or an acetyl group, Me represents a methyl group, and n represents an integer from 0 to 3;
(2) A fragrance composition comprising, as an active component, a fragrance material comprising one or more types of 2-cyclohexyl-1,1-dimethyl ethanol derivatives as described in the above item (1);
(3) An aromatic bleaching composition comprising a fragrance composition described in the above item (2).
The above, and other objects, features, and advantages of the present invention will become apparent from the following description read in conjunction with the accompanying drawings, in which like reference numerals designate the same elements.
Each of the following compounds are concrete examples of the 2-cyclohexyl-1,1-dimethyl ethanol derivative represented by formula (1) in each of the above described embodiments:
2-cyclohexyl-1,1-dimethyl ethanol;
2-cyclohexyl-1,1-dimethyl ethyl acetate;
2-(2-methylcyclohexyl)-1,1-dimethyl ethanol;
2-(2-methylcyclohexyl)-1,1-dimethyl ethyl acetate;
2-(3-methylcyclohexyl)-1,1-dimethyl ethanol;
2-(3-methycyclohexyl)-1,1-dimethyl ethyl acetate;
2-(4-methylcyclohexyl)-1,1-dimethyl ethanol;
2-(4-methylcyclohexyl)-1,1-dimethyl ethyl acetate;
2-(2,3-dimethylcyclohexyl)-1,1-dimethyl ethanol;
2-(2,3-dimethylcyclohexyl)-1,1-dimethyl ethyl acetate;
2-(2,4-dimethylcyclohexyl)-1,1-dimethyl ethanol;
2-(2,4-dimethylcyclohexyl)-1,1-dimethyl ethyl acetate;
2-(2,5-dimethylcyclohexyl)-1,1-dimethyl ethanol;
2-(2,5-dimethylcyclohexyl)-1,1-dimethyl ethyl acetate;
2-(2,4,6-trimethylcyclohexyl)-1,1-dimethyl ethanol; and
2-(2,4,6-trimethylcyclohexyl)-1,1-dimethyl ethyl acetate.
Among the compounds given as examples above, as well as others generically embodied in the present invention, there may be a plurality of isomers, including stereoisomers and optical isomers, based upon the methyl group substitution(s) on the cyclohexane ring. Any of these isomers, or a mixture of several of these isomers are useful in the present invention.
The above described 2-cyclohexyl-1,1-dimethyl ethanol derivatives all have a distinctive green floral scent. It has been observed that alcohols have a fresher scent nuance, and acetates have more of a rose scent nuance.
The 2-cyclohexyl-1,1-dimethyl ethanol derivatives of the present invention can be manufactured by, for example, the Grignard reaction described in Shinjikken Kagaku Kouza (published by Maruzen Corp. Ltd.), volume 14: pages 512-514, acetylation reaction described in the same, volume 14: pages 1014-1016, and hydrogenation reaction described in the same, volume 15: pages 426-428, each of which is herein incorporated by reference. Stated more concretely, the 2-cyclohexyl-1,1-dimethyl ethanol derivatives of the present invention can be manufactured by following the following reaction steps. 
wherein Me represents a methyl group, Ac represents an acetyl group, X represents a halogen, and n is an integer from 0 to 3.
In the manufacture method for the 2-cyclohexyl-1,1-dimethyl ethanol derivative of the present invention according to the above reactions, first, a Grignard reagent, that is prepared, in an ether solvent such as tetrahydrofuran, diethyl ether, or the like, from magnesium metal and the starting substance of a halogenated benzyl, represented by general formula (2), is reacted with acetone. Normally, the reaction temperature is at xe2x88x9210xcx9c50xc2x0 C., and preferably at 0xcx9c30xc2x0 C. As a result, a benzyl alcohol represented by the general formula (3) is obtained.
Next, by reducing the resulting benzyl alcohol (3) using hydrogen gas in the presence of a hydrogenation catalyst, an alcohol compound of the present invention represented by general formula (4) is obtained. This reaction can proceed without a solvent, but alcohol solvents such as ethanol or methanol and the like, hydrocarbon solvents such as hexane or heptane and the like, ester solvents such as ethyl acetate or butyl acetate and the like can be selected and used as appropriate. Examples of hydrogenation catalysts used in this reaction include Raney(copyright) nickel, ruthenium/silica, ruthenium/alumina, rhodium/silica, rhodium/alumina, palladium/carbon, and the like. The normal reaction temperature is 0xcx9c200xc2x0 C., preferably 50xcx9c150xc2x0 C. The normal hydrogen pressure is about 1xc3x97106 paxcx9c2xc3x97107 pa, preferably about 5xc3x97106 paxcx9c1.5xc3x97107pa.
Next, the alcohol represented by general formula (4) is acetylated using an acetylating reagent such as acetic anhydride or acetyl chloride and the like in the presence of a base. As a result, an acetate compound of the present invention represented by general formula (5) is obtained. This reaction proceeds without a solvent, but a hydrocarbon solvent such as hexane or heptane, a halogen solvent such as methylene chloride and the like can be selected and used as appropriate. Examples of bases used in this reaction include amine compounds such as pyridine, triethylamine and the like. The reaction temperature is normally 0-200xc2x0 C., preferably 50-150xc2x0 C.
In the manufacture of the compound represented by the above formula (1) of the present invention, the following compounds have 0, 1, 2, or 3 substitution groups on the cyclohexyl group: 2-cyclohexyl-1,1-dimethyl ethanol; 2-(monomethyl substituted cyclohexyl)-1,1-dimethylethanol; 2-(dimethyl substituted cyclohexyl)-1,1-dimethyl ethanol; 2-(trimethyl substituted cyclohexyl)-1,1-dimethyl ethanol; and acetates of these. When manufacturing these compounds, benzyl chloride having a substitution format corresponding to each of the compounds is used as the starting substance, and the manufacturing is conducted according to the method described above.
The 2-cyclohexyl-1,1-dimethyl ethanol derivative of the present invention represented by formula (1) all have a distinctive green floral scent and have an excellent persistent scent. Among these, the alcohols have a fresher nuance, and the acetates have more of a rose nuance.
The 2-cyclohexyl-1,1-dimethyl ethanol derivate represented by the general formula (1) of the present invention can be used alone as a scent component, or one or two or more types can be used together. Furthermore, one or more types of the 2-cyclohexyl-1,1-dimethyl ethanol derivative of the present invention represented by formula (1) and one or more types of fragrance components that are conventionally known can be mixed and used as a fragrance composition.
Conventionally known fragrances cover a wide range of fragrances. For example, components described in xe2x80x9cPerfume and Flavor chemicalsxe2x80x9d by Arctander, S. (published by the author, Montclair, N.J. (USA) 1969) can be selected and used as appropriate. Among these, representative compounds include alpha-pinene, limonene, menthol, phenylethyl alcohol, styrallyl acetate, eugenol, rose oxide, linalool, benzaldehyde, muscone, and the like.
When preparing a fragrance composition containing as the active components fragrances comprising one or more types of 2-cyclohexyl-1,1-dimethyl ethanol derivatives of the present invention represented by formula (1), although it will depend on the objective and the types of fragrances that are used, normally the compound is mixed at from about 0.01 to about 50 weight % and preferably from about 0.1 to about 20 weight % with respect to the target fragrance composition.
The 2-cyclohexyl-1,1-dimethyl ethanol derivative of the present invention represented by formula (1) is used in various perfume products and sanitation products that require the addition of fragrances. Not only does the present invention show high stability in these base materials, but the scent can be added without losing the activity of bleaching components, such as hypochlorites, percarbonate, perborate, hydrogen peroxide, and the like.
Furthermore, the fragrance composition, containing as the active components a single fragrance comprising the 2-cyclohexyl-1,1-dimethyl ethanol derivative or a fragrance of a mixture of two or more types, can be added and used in medical products and home products including various perfume products and sanitation products. The present invention results in increased diffusivity and preservation of the scent, while, at the same time, providing a new and pleasing scent.
Stated more concretely, the present invention can be used widely in shampoos, conditioners, perfumes, colognes, hair tonics, hair creams, pomades, hair cosmetic materials, other cosmetic materials or cosmetic cleansers, room fragrances, soaps, dishwashing detergents, laundry detergents, softeners, disinfecting cleaning agents, deodorizing cleaning agents, furniture care materials, disinfectants, bacteriacidal agents, repellants, bleaching agents, and other sanitation cleaning agents, toothpaste, mouthwash, toilet paper, odor giving agents to aid in the taking of medication, and the like. It is anticipated that the addition of the fragrance composition of the present invention will increase the value of these products.
Embodiments of the present invention will be described in further detail with embodiments, but the present invention is not limited to these embodiments.